US4973715AExpiredUtility

Furan polyols

49
Assignee: CENTRE SCIENT TECH BATIMENTPriority: Dec 12, 1986Filed: Dec 10, 1987Granted: Nov 27, 1990
Est. expiryDec 12, 2006(expired)· nominal 20-yr term from priority
Inventors:Gabriel RouxJanine RiveroAlessandro Gandini
C08G 18/6765C07D 307/46C07D 307/68C07D 307/42C08G 2115/02
49
PatentIndex Score
9
Cited by
1
References
49
Claims

Abstract

This invention relates to novel furan polyols, which are characterized in that they are the product of reaction of a strain selected from the group or consisting of a polyalcohol, a monoamine or polyamine, said polyalcohol or said amine possibly containing a furan cycle and mixtures thereof with a chain extension agent constituted by an organic epoxide, with the proviso that this organic epoxide is a furannic oxiran when this polyalcohol does not contain a furan cycle with the exclusion of 2,5(bis-hydroxy)furan as sole strain, when the chain extension agent does not contain any furan cycle. These furan polyols are used for the preparation of polyurethane foams having improved properties.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A furan polyol comprising the reaction product of: (a) an initiator compound selected from the group consisting of a polyalcohol, a monoamine, a polyamine, and mixtures thereof; and   (b) an organic epoxide chain extension agent, said initiator compound containing at least one furan moiety other than exclusively 2,5 bis-(hydroxymethyl)furan moieties when said chain extension agent is furan moiety free, and said chain extension agent being a furan-containing epoxide when said initiator compound is furan moiety free.   
     
     
       2. The furan polyol according to claim 1, wherein said polyalcohol is a C 1  -C 4  aliphatic polyalcohol. 
     
     
       3. The furan polyol according to claim 2, wherein said aliphatic polyalcohol is selected from the group consisting of ethylene glycol, propylene glycol, glycerine, trimethylolpropane, pentaerythritol and sorbitol. 
     
     
       4. The furan polyol according to claim 1, wherein said amine or polyamine is primary or secondary and contains at least one hydroxy functionality. 
     
     
       5. The furan polyol according to claim 1, wherein said initiator compound is obtained by the reaction of a mono or polyamine with an epoxide chain extension agent. 
     
     
       6. The furan polyol according to claim 1, wherein said organic epoxide chain extension agent is propylene oxide. 
     
     
       7. The furan polyol according to claim 1, wherein said organic epoxide chain extension agent is a furan-containing epoxide. 
     
     
       8. The furan polyol according to claim 7, wherein said furan-containing epoxide corresponds to the formula: ##STR11## wherein R 1 , R 2 , and R 3  is H, C 1  -C 5  alkyl group, C 1  -C 4  aliphatic alcohol group, C 1  -C 4  aliphatic acid group, C 1  -C 5  alkyl ester group, C 1  -C 4  aliphatic ketone group, C 1  -C 4  aliphatic aldehyde group or mixtures thereof and (X) is an organic radical. 
     
     
       9. The furan polyol according to claim 8, wherein said organic radical is a C 1  -C 10  aliphatic radical. 
     
     
       10. A furan polyol comprising the reaction product of (a) a polyalcohol initiator compound,   (b) a furan containing epoxide chain extension agent, thereby having pending furan moieties in the furan polyol reaction product.   
     
     
       11. A furan polyol comprising one reaction product of: (a) an initiator compound comprising a polyalcohol; and   (b) an organic epoxide chain extension agent, said polyalcohol corresponding to the formula: ##STR12## wherein R 1 , R 2 , and R 3  is H, C 1  -C 5  alkyl group, C 1  -C 4  aliphatic alcohol group, C 1  -C 4  aliphatic acid group, C 1  -C 5  alkyl ester group, C 1  -C 4  aliphatic ketone group, C 1  -C 4  aliphatic aldehyde group or mixtures thereof;   np32 0 to 10, provided that when n=0, at least one of the R 1 , R 2 , R 3  is a group with alcohol function, R 1  not being able to be CH 2  OH if the chain extension agent does not contain a furan cycle.   
     
     
       12. The furan polyol according to claim 11, wherein n is 1 to 10. 
     
     
       13. The furan polyol according to claim 12, wherein n is 1 to 3. 
     
     
       14. The furan polyol according to claim 11, wherein R 1  is H, CH 3  or CH 2  OH and when R 1  is CH 2  OH, n=1 to 10, R 2  is H, a C 1  -C 5  alkyl group, C 1  -C 4  aliphatic alcohol group, C 1  -C 4  aliphatic acid group, C 1  -C 5  alkyl ester group, C 1  -C 4  aliphatic ketone group, C 1  -C 4  aliphatic aldehyde group or mixtures thereof; and R 3  is H or a C 1  -C 5  alkyl group. 
     
     
       15. The furan polyol according to claim 14, wherein R 3  is a C 1  -C 3  alkyl group. 
     
     
       16. The furan polyol according to claim 15, wherein R 3  is CH 3  or C 2  H 5 . 
     
     
       17. The furan polyol according to claim 11, wherein said polyalcohol corresponds to the formula: ##STR13## wherein n is 1 to 10. 
     
     
       18. The furan polyol according to claim 11, wherein said organic epoxide chain extension agent is a furan-containing epoxide. 
     
     
       19. The furan polyol according to claim 18, wherein said furan-containing epoxide corresponds to the formula: ##STR14## wherein R 1 , R 2 , and R 3  is H, C 1  -C 5  alkyl group, C 1  -C 4  aliphatic alcohol group, C 1  -C 4  aliphatic acid group, C 1  -C 5  alkyl ester group, C 1  -C 4  aliphatic ketone group, C 1  -C 4  aliphatic aldehyde group or mixtures thereof and (X) is an organic radical. 
     
     
       20. The furan polyol according to claim 11, wherein said organic epoxide chain extension agent is propylene oxide. 
     
     
       21. A furan polyol comprising the reaction product of: (a) an initiator compound comprising a monoamine or a polyamine; and   (b) an organic epoxide chain extension agent, said initiator containing at least one pending furan moiety when said chain extension agent is furan moiety free and said chain extension agent being a furan containing epoxide when said initiator is furan moiety free, thereby having pending furan moieties in the furan polyol.   
     
     
       22. The furan polyol according to claim 21, wherein said organic epoxide chain extension agent is propylene oxide. 
     
     
       23. The furan polyol according to claim 21, wherein said organic epoxide chain extension agent is a furan-containing epoxide. 
     
     
       24. The furan polyol according to claim 23, wherein said furan-containing epoxide corresponds to the formula: ##STR15## wherein R 1 , R 2 , and R 3  is H, C 1  -C 5  alkyl group, C 1  -C 4  aliphatic alcohol group, C 1  -C 4  aliphatic acid group, C 1  -C 5  alkyl ester group, C 1  -C 4  aliphatic ketone group, C 1  -C 4  aliphatic aldehyde group or mixtures thereof and (X) is an organic radical. 
     
     
       25. The furan polyol according to claim 24, wherein said organic radical is a C 1  -C 10  aliphatic radical. 
     
     
       26. A furan polyol comprising the reaction product of: (a) an initiator compound selected from the group consisting of a primary monoamine, a primary polyamine, a secondary monoamine, a secondary polyamine, a hdyroxylated tertiaryamine containing at least two hydroxy functions,   (b) a furan-containing organic epoxide chain extension agent thereby having pending furan moieties in the furan polyol reaction product.   
     
     
       27. A furan polyol comprising the reaction product of (a) an initiator compound comprising an aminated polyalcohol obtained by reacting an amine other than a tertiary amine with a furan-containing epoxide, and   (b) an organic epoxide chain extension agent, thereby having pending furan moieties in the furan polyol reaction product.   
     
     
       28. A furan polyol comprising the reaction product of: (a) an initiator compound comprising an amine selected from the group consisting of NH 3 , methylamine, methylenediamine, ethylamine, ethylenediamine, propylamine, 1,3-propyldiamine, EDTA, and triethanolamine, and   (b) a furan-containing epoxy compound thereby having pending furan moieties in the furan polyol.   
     
     
       29. A furan polyol comprising the reaction product of (a) an initiator compound comprising a polyalcohol corresponding to the formula: ##STR16## wherein R 1 , R 2 , and R 3  is H, C 1  -C 5  alkyl group, C 1  -C 4  aliphatic alcohol group, C 1  -C 4  aliphatic acid group, C 1  -C 5  alkyl ester group, C 1  -C 4  aliphatic ketone group, C 1  -C 4  aliphatic aldehyde group or mixtures thereof; n=1 to 10; and   (b) an organic epoxide chain extension agent, thereby having pending furan moieties in the furan polyol reaction product.   
     
     
       30. The furan polyol according to claim 29, wherein n is 1 to 3. 
     
     
       31. The furan polyol according to claim 29, wherein R 1  is H, CH 3  or CH 2  OH, R 2  is H, a C 1  -C 5  alkyl group, C 1  -C 4  aliphatic alcohol group, C 1  -C 4  aliphatic acid group, C 1  -C 5  alkyl ester group, C 1  -C 4  aliphatic ketone group, C 1  -C 4  aliphatic aldehyde group or mixtures thereof; and R is H or a C 1  -C 5  alkyl group. 
     
     
       32. The furan polyol according to claim 31, wherein R 3  is a C 1  -C 3  alkyl group. 
     
     
       33. The furan polyol according to claim 32, wherein R 3  is CH 3  or C 2  H 5 . 
     
     
       34. A furan polyol comprising the reaction product of: (a) an initiator compound comparing a polyalcohol of formula: ##STR17## wherein n is 1 to 10, and (b) an organic epoxide chain extension agent thereby having pending furan moieties the furan reaction product.   
     
     
       35. The furan polyol according to claim 29, wherein said organic epoxide chain extension agent is a furan-containing epoxide. 
     
     
       36. The furan polyol according to claim 35, wherein said furan-containing epoxide corresponds to the formula: ##STR18## wherein R 1 , R 2 , and R 3  is H, C 1  -C 5  alkyl group, C 1  -C 4  aliphatic alcohol group, C 1  -C 4  aliphatic acid group, C 1  -C 5  alkyl ester group, C 1  -C 4  aliphatic ketone group, C 1  -C 4  aliphatic aldehyde group or mixtures thereof and (X) is an organic radical. 
     
     
       37. The furan polyol according to claim 29, wherein said organic epoxide chain extension agent is propylene oxide. 
     
     
       38. A furan polyol comprising the reaction product of: (a) an initiator compound selected from the group consisting of a polyalcohol, a monoamine, a polyamine, and mixtures thereof; and   (b) an organic epoxide chain extension agent, said epoxide chain extension agent being a furan-containing epoxide, thereby having pending furan moieties in the furan polyol reaction product.   
     
     
       39. The furan polyol according to claim 38, wherein said polyalcohol is a C 1  -C 4  aliphatic polyalcohol. 
     
     
       40. The furan polyol according to claim 38, wherein said aliphatic polyalcohol is selected from the group consisting of ethylene glycol, propylene glycol, glycerine, trimethylolpropane, pentaerythritol and sorbitol. 
     
     
       41. The furan polyol according to claim 38, wherein said amine or polyamine is primary or secondary and contains at least one hydroxy functionality. 
     
     
       42. The furan polyol according to claim 38, wherein said initiator compound is obtained by the reaction of a mono or polyamine with an epoxide chain extension agent. 
     
     
       43. The furan polyol according to claim 38, wherein said furan-containing epoxide corresponds to the formula: ##STR19## wherein R 1 , R 2 , and R 3  is H, C 1  -C 5  alkyl group, C 1  -C 4  aliphatic alcohol group, C 1  -C 4  aliphatic acid group, C 1  -C 5  alkyl ester group, C 1  -C 4  aliphatic ketone group, C 1  -C 4  aliphatic aldehyde group or mixtures thereof and (X) is an organic radical. 
     
     
       44. The furan polyol according to claim 43, wherein said organic radical is a C 1  -C 10  aliphatic radical. 
     
     
       45. A furan polyol comprising the reaction product of: (a) an initiator compound comprising a tertiaryamine being the reaction product of a furan free amine and furannic oxiran, and   (b) an organic epoxide chain extension agent, thereby having pending furan moieties in the furan polyol.   
     
     
       46. The furan polyol according to claim 45, wherein said organic epoxide chain extension agent is propylene oxide. 
     
     
       47. The furan polyol according to claim 45, wherein said organic epoxide chain extension agent is a furan-containing epoxide. 
     
     
       48. The furan polyol according to claim 47, wherein said furan-containing epoxide corresponds to the formula: ##STR20## wherein R 1 , R 2 , and R 3  is H, C 1  -C 5  alkyl group, C 1  -C 4  aliphatic alcohol group, C 1  -C 4  aliphatic acid group, C 1  -C 5  alkyl ester group, C 1  -C 4  aliphatic ketone group, C 1  -C 4  aliphatic aldehyde group or mixtures thereof and (X) is an organic radical. 
     
     
       49. The furan polyol according to claim 48, wherein said organic radical is a C 1  -C 10  aliphatic radical.

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